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OBJECTIVE To study the triterpenoid saponins from Anemone rivularis var. flore-minore and their antitumor activities. METHODS The n-butanol extract of 70％ ethanol extract from rhizome of the plant was separated. The triterpenoid saponins were separated and purified by normal silica gel column chromatography ，reversed phase ODS column chromatography ， Sephadex LH- 20 gel column chromatography and semi-preparation high performance liquid chromatography. The structures of these saponins were identified by spectral analysis （NMR and MS ）and physical and chemical properties. MTT assay was used to test the proliferation inhibitory activity of the compounds against five kinds of human tumor cells （HL-60 cells，A549 cells，HepG2 cells，HeLa cells and U 87MG cells ）. The apoptosis inducing effect of compound 7 on U 87MG cells was evaluated by flow cytometric Annexin V-FITC/PI staining test. RESULTS：Sixteen triterpenoid saponins were obtained and identified as 3 β-O-β-D-xylopyranosyl-（1→2）-α-L-arabinopyranosyl-oleanolic acid-28-O-α-L-rhamnopyranosyl- （1→4） -β-D-glucopyranosyl-（1→6）-β-D-glucopyranoside（1），3β-O-L-arabinopyranosyl oleanolic acid- 28-O-β-D-glucopyranoside（2），saponin B （3）， 163.com oleanolic acid- 3β-O-β-D-glucopyranosyl-（1→2）-α-L-arabino- pyranoside（4），HN-saponin F （5），clematoside S （6），prosapogenin CP 4（7），cussonside B （8），pulsatilla saponin C （9）， clemastanoside D （10），3 β-O-β-D-glucopyranosyl-（1→2）-β-L-arabinopyranosyl-hederagenin-28-O-β-D-glucopyranoside（11）， ciwujianoside C 3（12），ciwujianoside A 1（13），huzhangoside D （14），kalopanaxsaponin B （15）and hederacolchiside E （16）. Compounds 3，4，6-9 displayed inhibitory activities on the proliferation of tumor cells to different extent ，and compound 7 had the strongest activity ；compound 7 induced the apoptosis of U 87MG cell so as to inhibit the proliferation of cancer cells in a time-dependent manner. CONCLUSIONS The obtained 16 saponins are all identified as oleanolane-type ，among which compound 1 is a new compound. The monodesmosidic saponins ，the sugar chain of which attached at C- 3 and a free carboxyl at C- 28， possess stronger antitumor activity than others.
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Objective: To investigate the chemical constituents of the barks and stems of Melaleuca alternifolia and its antitumor activities. Methods: The chemical constituents were separated and purified consecutively by silica gel, Sephadex LH-20 column chromatography, recrystallization as well as preparative HPLC. Their structures were determined by physicochemical properties and spectral analyses. Furthermore, the cytotoxicity of some compounds against PC-9 (human non-small cell lung cancer cell line), HT29 (human colon cancer cell line) and MCF-7 (human breast cancer cell line) were tested by CCK8 method. Results: Eleven compounds were isolated and identified as ursolic acid 3-O-β-cis-caffeate (1), ursolic acid 3-O-β-trans-caffeate (2), tricontyl ferulates (3), 3-O-acetyl-11(12)-en-urs-28,13β-olide (4), 3-O-acetyl-ursolic acid (5), tricontyl caffeate (6), ursolic acid (7), n-nonacosanol (8), urs-12(13)-en-3-one-28-oic acid (9), 3β-O-acetyl-11α,12α-epoxy-oleanane-28,13β-olide (10), and betulin (11). Conclusion: Compound 1 and 2 are cis-trans isomers. Compound 1 is isolated from natural product for the first time, all the compounds are isolated from this plant for the first time except for compound 11. Compound 1 exhibited moderate inhibited effect on the proliferation of three human cancer cell lines.
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Objective: To study the antitumor constituents from Chloranthus fortunei. Methods: Various chromatographic techniques and spectroscopic methods were applied to investigate the chemical constituents from C. fortunei, and some of the compounds were screened for their antitumor activities by MTT method. Results: Sixteen compounds were obtained from the whole plants of C. fortunei and identified as rosmarinic acid (1), 2’-hydroxy-4,3’,4’,6’-tetramethoxychalcone (2), flavokawain A (3), cycloshizukaol A (4), atractylenolide III (5), 4β-hydroxy-8,12-epoxyeudesma-7,11-diene-1,6-dione (6), (8α)-6,8-dihydroxycadina-7 (11),10 (15)-dien-12-oic acid γ-lactone (7), curcolonol (8), 11-hydroxyldrim-8,12-en-14-oic acid (9), friedelin (10), isovanillic acid (11), 6β-hydroxystigmast-4-en-3-one (12), 3,4-dihydroxybenzoic acid (13), shikimic acid (14), scopolin (15) and N-acetyltyramine 1-O-β-D-glucoside (16). Compounds 4 and 5 showed weak cytotoxicity with IC50 ranged from 46 to 85 μmol/L. Conclusion: Compounds 2, 10, 11, and 13-15 are obtained from the genus Chloranthus for the first time and compounds 1-3 and 6-16 are isolated from C. fortunei for the first time. Some sesquiterpenoids from C. fortunei exhibited weak antitumor activities.
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Objective: To study the chemical constituents of the roots and rhizomes of Veratrum grandiflorum and its antitumor activities. Methods: The compounds were isolated and purified by silica gel, C-18 reversed phase column chromatography, and their structures were identified by MS and NMR analyses. The cytotoxic activities of compounds 1-6 against HepG2 (human liver cancer cell line) were evaluated by MTT method. The effect of compound 3 on cell apoptosis of HepG2 was detected by flow cytometry. Results: Eight steroidal alkaloids were isolated and their structures were identified as (3S,15S)-3β-angeloyl-15α-acetylzygadenine (1), epirubijervine (2), veratramine (3), jervine (4), 3-angeloylzygadenine (5), veratrosine (6), veramitaline (7) and veralkamine (8). Conclusion: Compound 1 is a new alkaloid, compounds 7-8 are isolated from this plant for the first time. Compound 3 showed moderate cytotoxic activity against human tumor cell line HepG2 with IC50 value of (13.70 ± 0.99) μmol/L, and induced early apoptosis of HepG2 cells.
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Objective::To screen out active fraction from Euphorbia fischeriana, separate active components from E. fischeriana and explore structure-activity relationships, in order to analyze and identify chemical compositions of petroleum ether fraction from E. fischerian ethanol extract by ultra-performance liquid chromatography with quadrupole-time-of flight mass spectrometry (UPLC-Q-TOF-MS). Method::The anti-tumor activities of petroleum ether, ethyl acetate, n-butanol and water extracts from E. fischeriana were tested by methyl thiazolyl tetrazolium(MTT)method. A variety of modern chromatographic separation methods were used to separate active compounds from petroleum ether layer. Compounds were isolated. Their structures were identified by NMR technique. The structure-activity relationships between anti-tumor activities and structures of compounds were investigated. UPLC-Q-TOF-MS technique was used to identify the structures of petroleum ether extract from E. fischeriana. Mass spectrometry was performed in the positive ion mode using ESI ion sources. Result::Six compounds were isolated from petroleum ether fraction. They were jolkinolide A, jolkinolide B, 17-hydroxyjolkinolide A, 17-hydroxyjolkinolide B, euphopilolide and atis-16-en-13(s)-hydroxy-3, 14-dione. A total of 23 peaks were identified based on the comparison of retention times, accurate masses and fragmentation patterns with available standard compounds and literatures. Among them, there were 19 diterpenoids, 2 polyphenols, 1 fatty acid and 1 triterpenoid. Peaks No.18 and No.21 were tentatively identified as new compounds. Conclusion::The petroleum ether fraction showed a potential anti-tumor activity. The structure-activity relationships were discussed. UPLC-Q-TOF-MS technology can be used to quickly and accurately identify the structures, so as to provide a reference for its quality evaluation and active ingredient research.
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Objective: To investigate the chemical constituents from Paris thibetica and their antitumor activities. Methods: The separations and purifications were taken by column chromatography over silica gel, Sephadex LH-20, ODS-C18, and semi-preparative HPLC. The in vitro antitumor activities of the isolated compounds were studied by MTT method. Results: Fourteen compounds were isolated from ethanol extract of the rhizomes of P. thibetica, which were identified as paris saponin V (1), paris saponin I (2), paris saponin II (3), paris saponin VI (4), pennogennin-3-O-α-L-arabinofuranosyl-(1→4)-β-D-glucopyranoside (5), paris saponin H (6), pennogennin-3-O-α-L-rhamnopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (7), paris saponin VII (8), parisyunnanoside G (9), trikamsteroside E (10), stigmasterol-3-O-β-D-glucopyranoside (11), β-sitosteryl palmitate (12), β-amyrin (13), and 4-hydroxy-5-methylfuran-3-carboxylic acid (14). Conclusion: All compounds are firstly reported from P. thibetica, and this is the first report of compounds 10 and 12-14 from the genus Paris L. Compounds 1-8 show cytotoxicities against BEL-7402. Among the tested compounds, compound 3 exhibits the strongest cytotoxicity with IC50 value of 0.48 μmol/L.
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Objecti ve To design and synthesize conjugates of alkoxylbiphenyl/C5-curcumine with antitumor activities. Methods Bicyclol,acetone and benzaldehyde with various substituents were used as raw materials. The target compounds were obtained by oxidizing and Aldol condensation reaction. And their antitumor activities were evaluated by MTS assay in the parental sensitive K562 and drug-resistant K562/A02 cell lines. Results Twelve alkoxylbiphenyl/C5-curcumine conjugates were prepared. Conclusion The synthetic procedure of the target compounds is simple,and the yield is high. Compound 3b could significantly inhibit K562 and drug-resistant K562/A02 cell proliferation,and the IC50 is 5.38 and 3.60μmol/L,respectively.
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As a kind of bioactive natural products with unique space structure, triterpenoid is widely used in diminishing inflammation, antibacterial, and protecting liver and kidney. Because of the strong ability of antitumor, it is likely to be developed as a new generation of anticancer drugs. In this review, the antineoplastic mechanism, structure-activity relationship, and pharmacophore improvement were summarized for further research on the antitumor properties of triterpenoid.
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Objective: To design and synthesize conjugates of alkoxylbiphenyl/C5-curcumine with antitumor activities. Methods: Bicyclol, acetone and benzaldehyde with various substituents were used as raw materials. The target compounds were obtained by oxidizing and Aldol condensation reaction. And their antitumor activities were evaluated by MTS assay in the parental sensitive K562 and drug-resistant K562/A02 cell lines. Results: Twelve alkoxylbiphenyl/C5-curcumine conjugates were prepared.
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This study was initiated in order to investigate the anticancer and immunomodulating activities of crude polysaccharides extracted in methanol, neutral saline, and hot water (hereinafter referred to as Fr. MeOH, Fr. NaCl, and Fr. HW, respectively) from the fruiting bodies of Panellus serotinus. Content of beta-glucan and protein in Fr. MeOH, Fr. NaCl, and Fr. HW extracts of P. serotinus ranged from 22.92~28.52 g/100 g and 3.24~3.68 g/100 g, respectively. In vitro cytotoxicity tests, none of the various fractions of crude polysaccharides were cytotoxic against sarcoma 180, HT-29, NIH3T3, and RAW 264.7 cell lines at the tested concentration. Intraperitoneal injection with crude polysaccharides resulted in a life prolongation effect of 23.53~44.71% in mice previously inoculated with sarcoma 180. Treatment with Fr. HW resulted in an increase in the numbers of spleen cells by 1.3 fold at the concentration of 50 microg/mL compared with control. Treatment with Fr. NaCl resulted in improvement of the immuno-potentiating activity of B lymphocytes by increasing the alkaline phosphatase activity by 1.4 fold, compared with control, at the concentration of 200 microg/mL. Among the three fractions, maximum nitric oxide (13.48 microM) was recorded at 500 microg/mL in Fr. HW. Production of tumor necrosis factor alpha, interleukin-1beta, and interleukin-6 was significantly higher, compared to the positive control, concanavalin A, at the tested concentration. Therefore, treatment with crude polysaccharides extracted from the fruiting body of P. serotinus could result in improvement of antitumor activity.
Subject(s)
Animals , Mice , Alkaline Phosphatase , B-Lymphocytes , Cell Line , Concanavalin A , Fruit , Injections, Intraperitoneal , Interleukin-1beta , Interleukin-6 , Life Support Care , Methanol , Nitric Oxide , Polysaccharides , Sarcoma 180 , Spleen , Tumor Necrosis Factor-alpha , WaterABSTRACT
Objective To study the antitumor components from an actinomycete strain(N2010-37)of bottom mud in Zhanjiang Mangrove,South China Sea.Methods The components were isolated and purified by chromatographic techniques and recrystallization,and the structures were identified by spectral methods together with physicochemical analyses.The antitumor effects of these components were tested in vitro by MTT method.Results Three compounds were identified including two anthrones and one novel lactone.They are(3S,4R,7R,8R,9S)-3,8-dihydroxy-4,7,9-trimethyl-2,6-cyclononanediolacetone(1),2-hydroxy-l-methoxy-3-methylanthraquinone(2),and 1,6,8-thihydroxy-3-methyl-anthraquinone(3).Conclusion Compound 1 is a new compound,and compounds 1 and 3 show the favorablecytotoxic activities against human chronic granulocytic leukemia cell line K562 strain by MTT method in vitro.
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Objective To determine the purity,composition and antitumor activities of polysaccharide AHP-12 from abalone harslet.Methods Its purity was checked by HPLC with TSK-GEL G4000PWXL column and agarose gel electrophoresis;Molecular weight was determined by gel filtration chromatography;Sulfate content was identified by gelatine nephelometry and aminohexose content by chromatometry;Gas chromatograph was applied to determine monosaccharide composition;Antitumor activities were investigated by MTT method.Results AHP-12 from abalone harslet was a homogeneous polysaccharide both measured by molecular weight and electric property;The molecular weight was about 3?105;It was contained sulfate 13.07% and aminohexose 4.98%;AHP-12 was composed of rhamnose,fucose and galactose(the ratio in mole is 1∶2.2∶1.7);the activity determined by MTT method showed it could hamper the growth of HeLa cell.Conclusion AHP-12 was extracted and purified from abalone harslet.It was a homogeneous polysaccharide,which contained sulfate and aminopolysaccharide,and with weak antitumor activities in vitro.
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Objective To investigate the chemcial constituents in Hedysarum polybotrys and their antitumor activities.Methods The chemical constituents were isolated by various column chromatographic methods,and their structures were elucidated mainly by NMR and MS evidences;Cytotoxicities of the purified compounds against human cancer cell lines HepG2 were evaluated by MTT method.Results Eleven compounds were isolated and identified as: n-tetracosanoic acid(Ⅰ),n-hexacosanic acid(Ⅱ),trioleic glyceride(Ⅲ),glycerol monopalmitate(Ⅳ),cetyl ferulate(Ⅴ),(+)syringaresinol(Ⅵ),7-hydroxy-4′-methoxyisoflavane(Ⅶ),isoliquiritigenin(Ⅷ),3-hydroxy-9-methoxypterocarpan(Ⅸ), ?-sitosterol(Ⅹ),and daucosterol(Ⅺ).Conclusion Compounds Ⅰ—Ⅳ and Ⅵ are isolated from this plant for the first time.Compound Ⅸ shows the inhibitory activity on HepG2 with IC50 values of 10.69 ?mol/L.
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AIM To study antitumor activity of melatonin in mice and its synergetic effects when MT combined with chemotherapeutic agents cytoxan(CTX). METHODS At a tolerable dose level,MT was administrated singlely or in combination with CTX to treat the transplanted murine solid tumor U 14 . The inhibition of tumor weight were observed. The weight of spleen and the hepatic cells' structure were also be measured. RESULTS The high dosed group of MT(80 mg?kg -1 ?d -1 ,sc) had a certain inhibition on the growth of the U 14 with inhibition rate of 27 1%. The low dosed group of MT(40 mg?kg -1 ?d -1 , sc) and the high dosed one combined with the CTX (25 mg?kg -1 ?d -1 ?1,ip) showed much pronounced than that of solely administration of MT. There was no significant influnce on the weight of spleen and the hepatic cells' structure. CONCLUSIONS The antitumor effect was observed by independent administration of MT. There was a synergism when MT combined with CTX but their toxicities were not obviously enhanced.